Sibbi Black-Briar is a Nordthief and a member of the Black-Briar family; his brother is Hemming Black-Briar, and his sister is Ingun. Maven Black-Briar is his mother. He was placed in prison after killing the brother of Svidi, his former fiancee. He asks you to locate Svidi. His mother had him thrown in prison to remind him that despite his privileged social status in Riften, he still answers to her and will be punished for any wanton acts that bring public shame on the Black-Briar name, as revealed in a note. As part of the quest Promises to Keep, you must visit Sibbi in the Riften Jail to learn more about the deal between him and Louis Letrush.

With not much to do in jail, Sibbi stands still in his cell 24 hours a day, without eating or sleeping, until you've completed Promises to Keep. After that, he'll sleep from 9am to 5pm, and can be found relaxing, eating, or taking a nap the rest of the time. Sibbi wears a set of fine clothes and a pair of fine boots. He is equipped with a leveled dagger which can be up to elven quality. He carries a selection of upper-class items and gold.

Sibbi is considered the worst of the Black-Briars, and is a common subject of conversation in Riften. When asked for word around town, Bee and Barb innkeeper Keerava will tell you: "Sibbi Black-Briar is furious that his ex-lover tried to murder him. He's leaving no stone unturned searching for her."Mjoll the Lioness will tell you about the black sheep of the Black-Briars: "Well, there's Ingun Black-Briar, Maven's daughter. Strange girl. She likes to spend time down in Elgrim's Elixirs working on her alchemy. Then you have Hemming, Maven's son; spoiled brat and heir to her empire. He follows her word like a loyal dog follows its master. And finally, Sibbi; the worst of all of them. He's in Riften Jail for murder." A conversation between Svana Far-Shield and Brand-Shei confirms that Sibbi recently was imprisoned, for murder, and that his betrothed, Svidi, was the cause:

"Svana, I heard that Sibbi was put in jail."

Brand-Shei: "Svana, I heard that Sibbi was put in jail. What happened?"Svana: "They say... well, they say he murdered someone. Something to do with Svidi."Brand-Shei: "Come to think of it, I haven't seen Svidi in a while. Wait... he didn't..."Svana: "No, it was Svidi's brother, Wulfur. She's in hiding now. Somewhere far from here I'd suspect."Brand-Shei: "If he wasn't a Black-Briar, I'd march right over to the jail and teach Sibbi some manners... but then I suppose I'd end up like Wulfur."

Meanwhile, a revealing conversation elsewhere will explain some of Svidi’s jealousy and the adultery committed by Sibbi. Inside Haelga's Bunkhouse, Svana and Haelga will have the following conversation.

"Sibbi and I are in love and you're just jealous!"

Svana: "Aunt Haelga, why you... demean yourself with these people you barely know? They show no real love for you."Haelga: "It's only a bit of fun. You're a lovely young thing, you should try it sometime."Svana: "No! I'm saving myself for someone special. Someone who loves me dearly."Haelga: "You mean Sibbi? You must be joking! All he wants to do is bed you and be done with it. You may as well get it over with and let him."Svana: "You're wrong! Sibbi and I are in love and you're just jealous!"

When you approach Sibbi in his jail cell, he will call out: "Have you come to gawk at me or is this a social call?" and "Ah finally, someone besides the stupid guards to talk to." If you are female, he will greet you with: "Well, well. Aren't you a sight for sore eyes. I've always got time for lovely ladies." He will then proudly tell you about his questionable family: "When speaking of the Black-Briars, only one thought should spring to mind. We are not to be trifled with. Help us, you end up rich. Cross us and you'll end up a memory. Is that enough information for you?" At this point he will exit conversation with: "Visit me anytime. I'm not going anywhere soon."

Even in Black-Briar Manor, they will discuss the imprisoned Sibbi, although in a more polite manner:

Maven: "Hemming, I need you to bring a note to Sibbi. I need him to do something for me."Hemming: "Sibbi? He's in prison... you put him there."Maven: "I know that! I can promise you when he's ready, he'll find the cell door unlocked."Hemming: "Why do you tolerate him, mother? All he contributes to this family is embarrassment and disgrace."Maven: "I tolerate your son because he'll do anything I ask, without question. I'd expect the same from my own son."

If you ask him for the reason for his imprisonment, he will tell you: "Look, we all have our flaws; mine is that women can't get enough of me. So I had this little affair going on while I was betrothed to a beautiful girl named Svidi. Well, she finds out and she tells her brother, Wulfur. Then her brother attacks me with a knife... I mean, I had to defend myself!" He will then admit being arrested for the kill: "Exactly! And now I have to stare at these bars for eight months. Can you believe it? I was about to let that wench marry into the richest family in Riften, and this is how she repays me. I'd do anything to have that whore's head on a platter. All I need to know is where she is." If you wish him ‘good luck’ he will just comment: "Amusing." If you offer to locate Svidi, he will instead say: "That's the spirit. Find her and I promise you'll be well compensated." When you ask him how he can get away with eight months for a murder, he will explain: "Mother thought I should be taught a lesson for airing the family's dirty laundry in public. I mean, I've... taken care of many people for her in the past. What in Oblivion did she expect me to do? Ah well. At least I have all the comforts of home during my stay. Well, except the touch of a woman of course." He will also reveal the limited information he has got on Svidi’s whereabouts: "She was a young woman... buxom, with long flowing black hair. She used to sing the most lovely songs to me when we were courting. I've never heard a voice so beautiful. All that talent will go to waste when I'm finished with her." This time he will end conversation with: "When I find that bitch, I'm going to wring her little neck."

Svidi turns out to have started a new life as the local bard at Vilemyr Inn in Ivarstead under the name Lynly Star-Sung. You can either persuade or intimidate her to tell the truth, and both options will make her plea: "Please, I beg you, don't tell Sibbi where I am. He'll kill me! Sibbi's been spreading lies about me, you must hear me out." She will then tell you her side of the story about Sibbi Black-Briar: "Sibbi and I were to be married. We were supposed to be happy together forever. Then I found that wretched poetry from Svana. When I confronted Sibbi about it, he threatened to kill me. I was scared so I told my brother Wulfur. He went to talk to Sibbi for me and... and... Sibbi killed him. My brother wasn't even armed! When I heard what Sibbi did, I fled. Now you've found me, and you're going to tell him where I am."

When you return from Lynly, Sibbi will greet you with: "Well, if it isn't my little problem-solver." When you tell him you have news about Svidi, he will respond: "Good, good. Just point me in the right direction and I'll do the rest." Three options will be available:

Option

Dialogue

She's in Ivarstead using the name Lynly.

"Ivarstead? So close to Riften? She's an even bigger fool than I thought."

She's made her way east into Morrowind.

"So, the whore thinks the Black-Briar reach ends at the border of Skyrim, eh? She'll soon discover her mistake."

Whichever option you choose between the first three, Sibbi will give you his key to a long chest containing moderately-valuable random loot, found in the basement (at the bottom of the stairs) of the Black-Briar Meadery in Riften, saying: "You've done me a great service, my friend. Allow me to compensate you for the information. This key opens one of my stashes in the basement of the meadery. Help yourself to any of its contents."

In the taproom of Bee and Barb is a regular, Louis Letrush, that mostly keeps to himself. However, if you get near him he will have a task at hand involving Sibbi: "Looking for work? I need someone to deliver a message to Sibbi Black-Briar." When asked about the message he will explain his problem: "Ah, well, I recently approached Sibbi Black-Briar about buying Frost, one of the finest breeding horses in Skyrim. He agreed to sell. I paid Sibbi half the cost of Frost up front, but before he could deliver, Maven had him locked up. Sibbi believes this exempts him from our deal. It does not. I want you to talk to Sibbi for me. Then, I want you to bring me Frost and the Lineage Papers that prove the horse's worth." He will then continue: "Head to the Riften jail and talk to Sibbi. Get him to tell you where Frost and his Lineage Papers are and bring them to me outside Riften. You'll be well paid for your time." You can then ask him to elaborate on a few things. When asked about why Sibbi is in jail, he will respond: "No idea, but whatever he did it must have angered Maven. No guard would lock up a Black-Briar without the old lady's permission." You can also ask why he doesn’t speak to Sibbi himself: "I'm not exactly... comfortable around guards or jails. Definitely not when associates of mine have been locked up. No, I'll meet you outside of town." He will finish the conversation with: "I'll meet you outside of town." or "Go on, then. Deliver my message to Sibbi."

When you approach Sibbi Black-Briar in his luxurious cell in Riften Jail and tell him Letrush sent you, he will respond: "Ah, and let me guess. He wants his horse. Well, that's going to be a bit of a problem. You see, I don't really outright 'own' Frost..." When you ask him if he doesn’t even own the horse, he will concur: "That is correct. You see, Frost belongs to the Black-Briar estate. Technically everything in the estate is owned by my mother, Maven. My plan was to take the horse from our lodge and deliver it to Letrush at the stables. Obviously, that didn't exactly work out as I'd planned... Still, I don't want to cross Letrush. Tell you what. Steal the horse and deliver it, and you can have the second half of the payment." At this point you can attempt to persuade him. If you fail, he will comment: "Nice try, but my mother's already got me in jail. Maybe you should try that one on Letrush." If you succeed he will offer you a key to a stash of gold: "Sure - take advantage of the guy in jail. Okay, fine. I can make the deal sweeter. I obviously don't have anything here, but... there's a hidden stash in the Lodge. And I did manage to hold on to the key... Take it." Lastly, you can just accept his offer and he will say: "Then I think we're done talking." However, you can still ask him what the logic of stealing Maven's horse is: "I'm not stealing anything. Besides, some jail time isn't going to make me roll over and play dead." At this point, you can choose to double-cross both Sibbi and Louis and go directly to Maven and tell her what is happening behind her back (note that this course of action will cause a slight bug). When confronted with the plot to steal Frost, Maven will say: "Don't tell me - Sibbi and Louis Letrush? Well, Sibbi is in jail and Letrush is certainly welcome to try. My hired help is more than a match for him." Lastly, you can seek advice from the leaders of the Thieves Guild, but to no avail. Brynjolf will say: "So Sibbi finally got the nerve to bare his teeth, eh? Look, this sounds like a family matter and I don't want the Guild in the middle of it. You do what you want. Just don't expect us to at your back when Maven has your head on the executioner's block.", while Delvin Mallory will say: "Guess I should have known. Maven and Sibbi have been at odds ever since she had him tossed into jail. Look, if I were you, I'd proceed carefully. Crossin' Maven is one of the first things you learn not to do when you're down here. As far as the Guild's concerned this is between Sibbi and Maven, so we're going to officially stay out of it."

Sometimes when you enter the cell, Sibbi may be sleeping on the inside side of his bed. When he wakes, he will be trapped between his bed and the wall. If you exit the prison and come back after a while, Sibbi will be sleeping on a bed in the next cell instead of his (you may leave him in right condition and awake but he still may end sleeping in the next cell).